By Amanda Kuhnert
When Erin Brennan had the opportunity to become a partner at Middleton, a women’s clothing and lifestyle boutique in Middlebury, she knew she needed guidance. “It was such a big decision—both from a financial and lifestyle standpoint,” she said. “I had people in my life who were advising me, but I needed someone unbiased.”
She reached out to the Vermont Small Business Development Center (VtSBDC) for support and was paired with longtime advisor Sarah Kearns. “One of the most important lessons she shared was the value of slowing down and taking things step by step,” Brennan said. “That approach allowed me to fully engage in the process, ask the right questions, and make well-informed decisions.”
A Partnership That Works
Brennan and her business partner, Elissa Kestner, met over a decade ago while working on Burlington’s Church Street Marketplace—Brennan landed there after returning home from college in Montreal. She quickly fell in love with fashion and styling, even briefly running her own personal styling business. “I’ve always believed that great style is about more than what you wear—it’s about how it makes you feel,” she said.
When Kestner approached her about becoming a partner, Brennan reluctantly agreed to visit the store—she had never envisioned herself owning a business—and ended up loving it. She was immediately drawn to the light, airy feel of the space and Middlebury’s charming downtown.
About six months in, Brennan said she’s enjoyed the transition from employee to owner. “When you own a business, you’re invested in a different way,” she said. “You get to try different things and then feel that sense of accomplishment when your hard work pays off.”
Her partnership with Kestner has been a strong fit as well. The two hold weekly meetings to keep each other informed. “We trust that the other person is going to handle what they say they’re going to handle,” Brennan said. While Brennan manages buying and day-to-day operations, Kestner oversees behind-the-scenes work, such as finances and long-term strategy.
“Finding a good partner is about a meeting of the minds,” VtSBDC advisor Sarah Kearns said. “Taking time to communicate clearly about your vision for the business and working to understand your partner’s vision—that goes a long way.”
Brennan hand-picks every item for Middleton, curating high-quality brands like Nation Los Angeles, Joseph Ribkoff, Citizens of Humanity, AGOLDE, and Pistola that reflect the boutique’s upscale, timeless style. She recently expanded the denim category as well, featuring popular labels such as AG Jeans. “We are thoughtful when selecting our merchandise and include items that are not only stylish and high-quality but also have meaning—whether that’s in the craftsmanship or the mission of the maker,” she said. Find them on Main Street in Middlebury or online at middletonvermont.com.
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